Break Into Pieces
by Zombie450AirBournePrincess
Summary: AU. Jess grew up with Liz and Jimmy in Hartford. He attends Chilton where he grows close to one Rory Gilmore. Jess's family life falls apart around him. He makes the choice to live else where. One man changes Rory's life with a huge impact. She has never met her father, the only man to be a father to her is none other than Luke Danes. Lit and JavaJunkie! Longer Summary inside!
1. Chapter 1

**A/N: I wasn't even gonna write this story or even tempt to write a GG fic. But the idea kept eating away at me and I broke down. It's all AU and I'll try to keep Rory and Jess as close to their characters as I can. Certain things will still be the same as on the show but other things are different. I didn't realize just how much I miss Gilmore Girls until I started to read stories on here and start to re-watch the series. Hate it or love it let me know.**

**Disclaimer: I own nothing related to Gilmore Girls.**

**Description: Jess grew up with both Liz and Jimmy in Hartford. He got accepted into Chilton with a scholarship only for it to be taken away when he spent too much time with Tristan pulling pranks. His home life slowly crumples around him, leaving Luke to pay for his schooling.**

**Rory lives with her mother and Luke. Lorelai knows about Luke paying for Jess's schooling but has yet to meet Jess. The only father Rory has ever known is Luke as Chris has never came to visit.**

* * *

Jess pulled the worn book from his back pocket sliding it across the table. A smirk graced his lips seeing the confusion in the clear blue eyes. "How'd you get my copy of Howl?" Came the small voice. Her blue eyes darting to the book moving back to the brown orbs.

"I found it yesterday." Jess replied seeing the confusion more evident in her eyes. She said nothing knowing it was in her bag all day yesterday. It was right between her folders and Chem. book all day long. That was until the bus ride home when it wasn't there to read.

"It never left my bag Jess." For a reply Jess shrug his shoulders stealing a fry from her tray and getting up. "You took it from my bag didn't you?" She asked annoyed. "Why?"

"Bored." He smirked walking away. Rory huffed stuffing her book in her bag before dealing with her tray. She tried to go after Jess groaning when the warning bells chimed for class. Instead she went to her locker getting the books she needed.

"Oh Mary." Rory refrained from rolling her eyes glancing at the blond boy who casually put his arm around her shoulders. "There's a party this weekend."

"So what Tristan." Rory bit at him trying to break from his grip.

"So?" He questioned pulling Rory into his side once again. "You're my date." He quipped with a smug smirk.

"Say what?" She screeched spinning to look at him. Tristan sent her a wink and walked off stuffing his hands in his pockets. The anger at what Tristan demanded of her was boiling in her veins. There was no way she was going to Tristan's party with him outta everyone.

She slammed her books on her desk her bag falling to the floor with a loud thud. She could feel eyes on her for a few seconds. After class started she felt a pair still on her. She glanced in the direction she knew Jess would be in. For a split second she could she worry in his dark eyes but that was covered up with a smugness smirk tugging on his lips.

"Ms. Gilmore," Was being called breaking the gaze she held with Jess. Rory blushed slightly looking at Max Medina, giving a small smile. "You will be working with Mr. Mariano." The smile Rory held turned into a grin. "Earnest Hemingway is the author you get to dissect for your oral report." The grin on Rory's face slipped into a frown of annoyance. Of all the authors out there she gets stuck with the one she truly despises. She didn't need to look back at Jess to know that he was happy as ever.

* * *

**~ 1 Year earlier ~**

Rory walked through the halls not knowing what to expect. Chilton was completely different than Star Hollows high. Between being called Mary all day long, her locker being stuck and wrecking Paris's project her day had been the worst day of her life. The only plus was when a boy with black hair and deep brown eyes sat at the table across from her at lunch. She glanced up from her Jane Austin novel to get a better look at the boy who sat at her table. He held a small smirk pulling a book of his own out and sat reading. Jess would glance at Rory when he felt her eyes where back on her book.

"Hi." Rory put her book down glancing at the boy before her.

"Hi." He replied his eyes following the words typed on the page he was on.

"I'm Rory." She told him trying to get the boy to say more.

"Jess." Half a smirk spread across his lips. He looked up in time to see Rory stand up. Normally Jess sat by himself to engrossed in his books to par take in a conversation that was based on rumors. But seeing the blue-eyed, brunette a book in front of her not caring about the people around her, he could tell she was different.

For the first two weeks of school Jess would take his time getting to the lunchroom. He would look at the sea of students until he found the one he was looking for. Everyday Rory tried to talk to him. All she would ever get was a grunt or huh.

"Why?" Rory asked finally having enough. Jess placed his unopened book on the table. He raised an eyebrow placing his arms on the table, giving her a questioning look. "Why do you insist on sitting here? You don't talk no matter how many times I try. God it's so annoying. I don't even know why I don't move elsewhere. Or why I let this bother me. But it does." Rory flushed a light shade of pink over her mini rant.

"It is what it is." Jess smirked seeing further frustration cross her face.

"What's that supposed to mean?" Rory huffed finding the tray of food more interesting than the boy who sat across from her.

"You tell me." He replied getting up walking around the time bending down to whisper. "There is no friend as loyal as a book." With that Jess walked off leaving a very confused Rory behind. That didn't answer her question at all. The words swam around in her head all weekend. She finally just gave up. She had a feeling Jess would never tell her. Outta mind, outta sight. She wanted to avoided him at all costs but quickly learned she couldn't do that, there was something about Jess that kept pulling her back in.

* * *

"I figured we could go to your place and get started on this report." Rory spoke up joining Jess in the hall way. She figured it would be easier to stay in Hartford for a few hours.

"Can't." Jess replied glancing at Rory. She in return eyed him up with a small glare. How was Jess supposed to explain that his mother was a drunk and his father decided 6 months ago that this life wasn't for him? That his uncle pays for him to be in Chilton. "We can go to yours though." He pointed out.

"Can't do that either. I have to be at my grandparents' house tonight and I was gonna head to the library to get some work done before hand." The dress she was to wear for the dinner hung in her locker.

"How did you get into this school?" Jess asked with a playful smirk on his lips. Rory gasped gently hitting him. "Ror if you were already heading to the library don't you think I could go with you?" He asked seeing the realization hit her.

"I didn't think of that." She said softly looking at the floor. Jess pulled her into his side. Letting the conversation drop. Rory had to wonder why Jess couldn't have been the guy that wanted to go to parties with her. The guy that liked her the same way she liked him. But according to Jess they were only friends. Being friends was nice but she wanted more and every day she saw the girls at school flirt with him it cut her deep.

The one thing Rory didn't know it had hurt him to see her with Dean. It was at that moment he decided it was best to stay friends with Rory. Even after Rory confessed to him that Dean had broken up with her because he had feelings for some Lindsey chick. He hated to see Rory so broken and fragile. He wouldn't be the cause of that ever. It was better if they stayed friends. He pushed his feelings away. No one could hold a candle to Rory Gilmore.


	2. Chapter 2

**I wanted to say thank you to everyone that has taken an interest in this story. I hope I did Luke and Lorelai justice with this chapter. Enjoy.**

**Disclaimer is on the first chapter, I don't own and I never will so it wont be changing ever so no need to repeat saying so on every chapter. Most of the flashback I used from Season 1 Episode 6 - Rory's Birthday Parties.**

* * *

"Seriously Luke all you have to do is call them and tell them between the Diner and the Inn I went missing. That some deranged man stole me." Lorelai huffed walking behind the counter to get a cup of coffee and a doughnut. Luke saw no use in shooing her to the other side of the counter so instead he handed her the tongs.

"Use these. No one in their right mind would kidnap you let alone keep you longer than a minute." Luke grumbled filling a few cups on the counter.

"But you did." Lorelai pointed out finishing her coffee.

"I didn't kidnap you. I married you. Huge difference Lor. Why did I marry you?" Luke shook his head pouring more coffee in his wife's cup.

"You asked, I said yes and the rest is history dear old Duke." Lorelai grinned drinking her coffee. Luke gave her a soft glare walking away from her shaking his head. Lorelai finished her coffee kissing her husband on her way out the door. She was already running late.

* * *

**4 years earlier**

_"She's not here yet." Luke said seeing Lorelai walk in with a garment bag._

_"All right. You'll have to entertain me until she arrives. OK, Burger Boy, dance." Lorelai grinned looking up at Luke from her stool._

_"Will you marry me?" He asked no emotion but there was something deep down hoping for more from the oldest Gilmore girl._

_"What?" Lorelai asked shocked. To her Luke had always been a friend, nothing more. But now that he asked ever so politely something had clicked in her head. It wasn't as if she had guys lined around the corner for her. And Luke was a good-looking man. "Sure why not, my calendar is free."_

_"Just looking for something to shut you up." Luke stood in his tracks a shocked expression on his face. "You have nothing better to do so you plan on marrying me?"_

_"You asked Luke, I'm just giving you an answer." She replied._

_"How about we start out with a date first?" Luke asked with a shaky breath._

_"You can be my date to Rory Gilmore's birthday celebration this Saturday night." Lorelai grinned batting her eye lashes at him._

_"You don't have to ask me, you know." He replied filling her cup with fresh coffee._

_"I know. But I would like you to come as my date." Lorelai beamed. She liked the way it rolled off her tongue._

_"Yeah?" Luke asked joy spreading through his body._

_"Yeah." She smiled at him._

_"OK, I'll see. After that I get to pick the next date." He smiled having it already planned in his head._

_"Great. 7:00. Don't be late." She told him joining Rory who had just came in._

* * *

"God Jess, I can't get through his books how am I suppose to get through a whole report?" Rory asked looking away from the computer screen. She had stared blankly at a page full of facts about Ernest Hemingway.

"You got me Ror." Jess replied writing things down. Rory huffed seeing he really didn't need to read up on him, but why should he?

"Just because you idolize the guy doesn't mean I can slack off and let you do all the work. 50/50 Jess." Rory turned to look at him.

"You can get through this Rory. Why don't you take a break and work on a few other things and once you have cleared your head come back to it." Rory sighed closing outta the Internet.

"I guess it wont hurt." Rory replied joining Jess at the table. Rory got so caught up in her other work she lost track of time until Jess poked her. "What Jess?"

"Shouldn't you be gone?" Rory looked at her watch. In a hurry she got up stuffing her work into her bag. She was lucky she had changed into her dress for dinner after school. She was already 5 minutes late. "I can give you ride." Jess offered getting his things together.

"No it's fine." Rory told him walking away. 10 minutes later Rory was ringing the door bell at her grandparents house, her mothers jeep already in the driveway.

"Please come in." Sophie said opening the door. "May I take your things?" Rory handed her things over. Sophie was a younger maid, she had been around for a month now. She had black hair and fair skin. "They're in having drinks." Rory smiled and walked in sitting by her mother.

"Sorry I'm late I was at the library doing some work. I lost track of time." Rory smiled sheepishly. Her grandma handed her a club soda.

"That's alright dear. School comes first." Emily replied.

"Gee I was 5 minutes late and I get a lecture on telling time and how I must always be early. My lovely daughter here is 15 minutes late and is off the hook." Lorelai piped in downing her martini astonished.

"Why were you late Lorelai?" Emily asked annoyed.

"Because traffic." Lorelai lied.

"You can't lie Lorelai. I know better than that. You were late because you didn't wanna be here and Rory is late because she was doing school work. That's a huge difference." Emily replied in a harsh tone.

"We really don't know if she was doing school work. She could've been with a boy doing things." Lorelai jumped up with an accusing finger at her daughter.

"Lorelai sit down she wasn't with a boy doing things." Emily huffed.

"She is my daughter, mother."

"I was with a boy. Jess in fact."

"Ha I told you." Lorelai cut Rory off.

"We were assigned partners for an oral report. We wanted to get a start on it." Rory finished watching her mother slump on the couch.

"Sorry I'm late. What did I miss?" Richard asked joining the girls.

"Nothing dad." Lorelai mumbled.

"Dinner is ready." Sophie announced. They all walked into the dinning room sitting in there normal spots. Throughout dinner they made small talk about how Rory was doing in school. A few insults on why Luke couldn't join them.

"Mom for the last time. He owns and runs his own business he can't get away just because you want him to suffer here for 2 hours." Lorelai was getting frustrated with her mother.

"I'm just saying Lorelai, he is apart of this family, is he not?" Emily asked putting her fork down.

"Yes mother. But every time he comes all you do is put him down. You don't like him. We all know this and oddly enough we're all ok with that. So why should he come here when you think he isn't good enough for me?" Lorelai asked staring at her mother. Emily only huffed.

"Well he isn't." She replied dryly.

"Grandma, grandpa I think we should be going now." Rory didn't want anyone to say something they would later regret.

"Rory's right. We should be going." Lorelai added getting up. Rory hugged her grandparents saying bye to both of them. Together Rory and Lorelai walked to the door getting their things.

"I figured we could do a movie night tomorrow." Lorelai spoke up for the first time 20 minutes into the car ride home.

"I'd love that and it gives me an excuse to stay away from Tristan's party tomorrow night. I couldn't possibly leave my mother alone to go into a sugar coma alone." Rory smirked happy she had an out.

"Now if you wanted to go to the party we could cancel until next week." Rory was quick to shake her head.

"Don't even joke about that mom." Rory was being dead serious.

"Note taken. Wanna go to Luke's?"

"He makes the same coffee at home." Rory protested. All she wanted to do was go home, not watch her mother fawn all over Luke.

"But it's not the same now is it?" Lorelai asked parking in front of the dinner. Rory agreed with her mom and together they headed inside.

"We're closed." Luke said hearing the bell jingle. He never looked up from his receipts though.

"Good thing I'm your wife then." Lorelai sat in the stool across from Luke sharing a small kiss with him. Luke got them coffee knowing better than to fight them on a Friday night.

"What happened?" Luke asked seeing the two sullen faces before him.

"I was late, got yelled at. My darling offspring was later than I was and she got a medal for it. Adolf hates you but expects you to be there every Friday night." Luke's face paled. "I wont make you suffer dear husband of mine." Luke only nodded.

"Uh I'm gonna head home, I'm beat." Rory finished her coffee and headed out the door, feeling it was necassery to leave them alone.

"Ok sweets." Lorelai called out to the now closing door. "My parents can think what they want Luke. I've never cared before and I know how uncomfortable they make you. I wont make you go." Luke sat feeling relieved until he heard the next words outta his wife's mouth. "Until next Friday, you have to come."

"No." Luke grumbled. Lorelai pouted looking at him. "Not gonna happen." She than started to whine a little. "If I do this you get decaf coffee all next week." Lorelai glared but gave in.

"Fine." She muttered getting up. "I'll see you at home." She kissed his cheek and headed out to her jeep.


	3. Chapter 3

**I had to change a few things around for this story. I personally didn't like the way I had written part of this chapter and chapter 4. A few things have changed with this one. As for chapter 4 most everything is going to be different. I'm sorry for this inconvenience.**

* * *

"Sweets what's the rush?" Mother asked daughter watching said daughter gulp her cup of coffee down with one huge gulp.

"No rush." Rory tried with a nervous look on her face. "Ok fine I gotta meet Jess at the bus stop in a few minutes." Rory relented seeing the look on her mom's face.

"The same Jess you were with yesterday? The Jess that made you late for Friday night dinner? The Jess that vandalized your book?"

"Yes the very same one. How observant of you." Rory mocked placing her hand over her heart.

"Don't mock mommy." Lorelai protested using a fry to point at Rory.

"How dare I do such a thing." Rory gasped getting up.

"Hey now you haven't touched your food." Lorelai pointed to the plate covered with fries and a burger that went untouched.

"I'm not hungry." Rory protested.

"Rory you gotta eat." Luke walked up behind her startling her making her jump. "Sorry, at least eat an apple."

"Ok daddy Luke." Rory grinned taking the apple from a grumbling Luke. She tried to make a run for the door.

"But she doesn't like apples dear husband of mine." Lorelai smirked being a tad dramatic. "Because it's healthy for you doesn't mean it wont kill Rory. Do you want her to die Luke?" Lorelai asked standing from the table a serious look on her face.

"I guess I'll have to go find my Prince now." Rory smirked finally able to walking the short distance to the door.

"Why would you think I wanted Rory dead? I want her to live a long and _healthy_ life." Luke stated over emphasizing healthy to prove his point.

"Sugar tell your father here you don't like apples." Lorelai placed her hands on her hips waiting for Rory to back her up. But that didn't happen.

"Sure I do." Rory protested taking a bite of the apple to prove her point. Luke was pleased with that, well Lorelai looked at her daughter shocked. He knew he couldn't fix her eating habits over night but this was a huge improvement. That's all Luke asked for. One day at a time. "Happy?" Rory asked walking out the door. The second she could she threw the apple in the trash sitting down on the bench to wait for Jess's bus. She pulled her book out to read well she waited but the voice she heard behind her was very cringe worthy. She focused on her book waiting for that voice to pass but she had no such luck.

"What a surprise." Rory rolled her eyes keeping them locked on the words that took her to world far away. "What? It's like that now?" Dean asked with a scoff.

"Like what Dean?" Rory was growing more agitated by the minute. "You broke up with me to be with Lindsay. You left me, I didn't leave you. So therefore I can act any way I want to." She hissed turning to look at him. She couldn't believe the nerve of him.

"Because you spent all your time in Hartford with Jess." He yelled shaking his head looking to see the black-haired boy approach them. "What was I supposed to think Rory?"

"That I wouldn't cheat on you. Jess is a friend." Rory yelled standing up her back to Jess. Who kept quiet watching the scene unfold in front of him. He would step in when he absolutely had too.

"Why is it so hard for you to admit that you like him? Scratch that you love him." Dean yelled walking off leaving Rory standing there confused on what had transpired. Did she love Jess? No that was just lunacy. Jess was her best friend. Even if she did love him in a more than friends way he couldn't possibly love her the same way.

"You ok Rory?" Jess asked taking the few steps to be by her side. She gave him a weak smile nodding. He wanted to put an arm around her to comfort her but he wasn't sure that he should. He didn't wanna upset her or confuse her even more.

"Wonderfully perfect." She muttered wondering just how much he had heard. "I figured we could go back to my house. Less distracting that way." Jess nodded letting Rory lead the way. A silence fell over them as they walked. Rory couldn't be in love with him? There was no way. Stealing a quick glance at her, Jess smiled to himself. Maybe she was in love with him, like he was with her. "I figured after we get a few things done we could go to Luke's and get a bite to eat. I could also show you around if you want." Rory suggested getting her things from her room well Jess got his from his bag.

"You don't have to. I think if I got lost I could find my way back. Bread crumbs and all." He smirked sitting at the kitchen table. He found it easy to ignore the town tour. He knew his way around. It wasn't that hard to do. "Luke's?" He questioned hiding his worry. He didn't want Rory to know about that part of his life. When he agreed to come here he totally spaced on Luke until it was far too late to do anything about it. He didn't want Rory to think less of him.

"Yea he's my step-dad and he has the best coffee and burgers around." Everything about that sentence shocked Jess. He knew Luke was married to woman who had a kid but he didn't think it was Rory. Jess knew that Luke was married to a Lorelai Danes. He never had to think they were one and the same after all Rory's last name was Gilmore. Seemed like things were gonna change. Now he could never date Rory seeing as she was his step-cousin. There was nothing right about that.

"Well maybe. Or we could just order in." Jess suggested.

"I kinda already promised my mom I would meet her at Luke's." Rory replied with an apologetic smile getting her notebook and computer ready. Jess slowly nodded needing to find a way to tell Rory that Luke was his uncle.

While he tried to figure out how to tell Rory all of this Lorelai was looking at her husband with a look of concern and amusement. Luke walked around in a world of his own. There had to be more than one Jess at Chilton. It couldn't be possible. Just because Stars Hollow was extremely small didn't mean Hartford was just as small. On the contrary Hartford was huge, a few Jess's had to be walking around.

"Who is Jess?" Luke asked putting his pad on the counter turning to get some coffee for his wife. "This crap is still gonna kill ya." He muttered looking out the windows.

"He's Rory's friend. Has been for a while now. Well ever since she started Chilton last year."

"He?" Luke asked convinced it was his nephew. He promised Jess that he would keep this a secret. Jess didn't want people to know and he had yet to tell anyone. The most he told Lorelai was that he was helping his sister pay for his nephew's school. A school that was like Chilton. What was he suppose to say?

"Luke you're starting to freaking me out. Want to enlighten me here?"

"It's just." Luke sighed removing his baseball cap running a hand through his hair replacing his hat. "I got work to do Lorelai." Luke replied walking into the kitchen leaving a very confused Lorelai behind.

"Uh yea I gotta check in at the Inn anyway. I'll see you later." Lorelai yelled walking out the door. She pushed her husband outta mind. He would explain things to her later when gossip wouldn't spread throughout town.

"He was freaking out over nothing. It doesn't make sense to me." Sookie replied after hearing Lorelai explain Luke's behavior. Sookie kept walking around the kitchen two or three guys following behind her making sure Sookie stayed in one piece along with the rest of them.

"There was never a Jess before I came along?" Lorelai asked filling a cup with coffee.

"I'm sorry hun but there wasn't. I don't know anyone by the name of Jess. You said he had a nephew." Sookie used her spoon to point at her friend.

"But why would he wig out?"

"Lorelai the phone is for you." Michel announced walking into the kitchen not giving Sookie time to reply. Lorelai took her cup of coffee and headed to the front desk. She wanted to deal with anything at the moment. Something was going on with her husband and it was eating away at her. Whatever it was couldn't be ignored.


	4. Chapter 4

_**I'm sorry that I had changed things around mostly Jess's secret about Luke being his uncle coming out but I have a different way I wanna do that, that I happen to like a lot more and I think you guys will to. Plus it works better for the story.**_

_**A quick thank you to everyone that has taken an interest in this story. It means a lot to me. A huge thank you to darkheadlights for volunteering to be my beta for this story.**_

* * *

"Rory can we uh talk for minute?" Jess asked wiping his hands on his jeans. With one look Rory could see that whatever Jess wanted to talk about was serious. She could see a faint line of sweat on his forehead. She found it strange to see Jess this nervous.

"Of course Jess. What's going on?" Rory laid her pencil on to top her notebook turning fully to Jess giving him her full attention. Jess licked his lips everything he needed to say was on the tip of his tongue. The phone started to ring beating him to the punch. "Hold your thought." Rory told him going to the living room to pick the phone up off the coffee table. "Hello?"

"Daughter of mine, you gotta fend for yourself tonight. A few things at the Inn came up." Lorelai was in panic mode. A pipe in room 10 had burst.

"That's fine. Gives me more time to get some work done." Rory replied. She quickly let her mom go. "You still want to order a pizza?" Rory asked walking back into the kitchen.

"Sure. What about Luke's?"

"Trouble at the Inn." Rory replied dialing the number to order pizza. Jess silently sighed to himself, relieved he didn't have to spill his secret yet. He wasn't ready for Rory to know how crappy his life has become. Rory wouldn't judge him, this he knew but he wasn't ready to open up about it. "About a half hour or so. Now what did you need to talk about?" Rory asked sitting at the table.

"You going to Tristan's party tonight?" Jess asked the first question that came to mind. He could've easily talked about books, movies or music but they were never a topic he had to ask Rory if he could talk about with her. Tristan's party was far enough away from any conversation about family. Plus he wanted to know.

"No. He thinks I'm going as his date. I've got plans to stay and watch movies with my mom. Are you going?" The question threw her off. Why was he so nervous before her mom called about Tristan's party? She was skeptical that this party was the main thing on his mind. But she was going to let it go.

"I was planning on it but now I don't see the point." Jess shrugged going back to his work. He was really enjoying this assignment on the great Hemingway. And just because he got to spend extra time with Rory, didn't hurt either.

"Why not?" Just because she wasn't going didn't mean he had to miss it, unless that meant...

"It wouldn't be fun without you." Rory let her thought go. Was that in a friend way or was there more behind it?

"Mom would understand if I canceled on her tonight. I only agreed to it so I wouldn't have to go with Tristan. I don't get how you could be friends with him."

"He's not that bad." Jess spoke up stopping Rory's rant. "We don't have to go, but it wouldn't suck if you came with."

"Oh thanks for that. Such a boost on my ego there. As long as you stay with me the whole time especially around Paris, it should be fun."

"All I wanna do is avoid Paris. I should probably head out and get ready then. I can come back and get you." Jess offered standing up.

"Only if you want to... or I can borrow my mom's jeep or I could..."

"Relax?" Jess questioned with a smirk getting her to stop. "I'll be back around 8 to get you." Rory nodded letting him get his things put in his bag.

A few hours later Rory found herself fighting with her clothes in her closet. It didn't matter how many times she looked through them she couldn't find anything to wear. Did she wanna make an impression on Jess? She didn't care how she looked for the rest of her classmates but she felt she had to look her best for Jess.

"Mom!" Rory yelled with a sigh tossing a shirt on the bed.

"What's wrong sweets?"

"I don't know what to wear." Lorelai picked a few things up and looked over them.

"Jeans or a skirt honey?" Rory shrugged. "Right, you can wear these jeans with this red top or you can wear this black skirt with this blue shirt. Grandma says blue brings the color of your eyes out." Chewing on her lips Rory took the skirt and blue shirt.

"Thanks Mom." Rory smiled pushing her mom out the door.

"Anytime, sweetie." Lorelai replied walking back to the living room.

"Since Rory is headed off for the night I figured we could go out as well." Luke suggested. With no one coming in after the early dinner rush Luke closed up early and came home.

"That sounds nice." Lorelai smiled. After her hectic day at the Inn with the pipe bursting, her mind running wild about what was wrong with her husband as of late, they needed tonight.

"Good. Go get ready."

Jess had snuck into his house only no one was there. He searched for his mom but she wasn't passed out any where. He figured she was off finding her next fix, a new guy or both. It had been the two of them for sometime now. When he left this morning she was still asleep. He wasn't going to worry about her whereabouts tonight though. Tonight was about having fun with Rory and forgetting about his family problems. He really wanted to run away. The only person keeping him put was Rory. There had to be a way he could run away and keep Rory close to him. He'd figure it out. He had too.

A few hours later found Jess and Rory on the dance floor, swaying back and forth to a slow song. "How did you talk me into this?"

"It was either this or I would annoy you with Ayn Rand for a month." A smirk spread across Rory's lips as she saw the disgusted look on his face. Suddenly Rory paled, pulling Jess closer to her. "Keep Tristan away from me. I will not dance with him."

"He can't steal my date from me. That would be unacceptable." Jess smirked seeing a pink tint forming on Rory's cheeks.

"Mary I'm happy you joined us, disappointed you didn't come with me." Tristan faked a pout his hand covering his heart.

"Get used to it, Tristan. She's with me now." Jess spoke with a hint of possessiveness behind it, his hold on Rory becoming more protective.

"Controlling are we?" Tristan smirked, walking off. Jess looked at Rory for the first time since Tristan walked up to them. The blank look on Rory's face made him really think about what he had said. Rory stayed quiet at a loss for words.

"Rory I didn't mean it like that." His words replayed in his head. How could he be such an idiot?

"Can you just take me home?" Rory asked, trying to process his words. What did he mean she was with him now? She wasn't anyone's toy or play-thing. Jess nodded, taking her hand in his, and they weaved their way through all the teens. "What did you mean Jess?" Rory asked once they were in his car headed for Stars Hollow.

"I don't know Rory. It just came out. I hate it when he hangs all over you." Was that jealousy that Jess had over Tristan? "You don't hate me do you?" Rory shook her head. She wouldn't get a better explanation out of him tonight and she was ok with that for now.

"Never." She gave him a weak smile letting her mind try to process what this meant for her and Jess. Was she going to let it ruin her friendship? Did he have the same feelings for her? Could things just go back to normal?


	5. Chapter 5

**It's important that you go back and reread chapters 3 and 4 if you haven't yet. Certain things wont make sense if you haven't. I changed things around for a reason. It really wasn't my intention but everything works out better this way, as you'll see at the end of this chapter.**

**Thanks to all the love so far with this story, it means a lot to me. **

**A huge prop to my beta for this story darkheadlights**

* * *

Wednesday came rather quickly. Rory had been avoiding Jess. She still wasn't sure what she wanted to do with Jess and what happened at Tristan's party. Part of her wanted to forget it ever happened but there was another part of her that told her Jess was only protecting her in the way a boyfriend would. The only problem Jess wasn't her boyfriend, just her friend. And she should have never put him in that spot to start out with. Instead of hanging out with Jess, Rory had been spending more time with Paris. After all, they were friends on a certain level. No matter how annoying and competitive Paris could be.

Jess let Rory have time to figure things out. He was busy trying to figure out a new place to live. Everything at home was really starting to take a toll on him. A few days without Rory was showing him just how much he needed her. He had to find a way to make it right. Jess sat down at the lunch table with Rory. It was time that they actually finish their oral report since it was due tomorrow. That was where he was going to start. Rory glanced up from her book. Not only was she shocked to see Jess, but happy as well. She had missed him.

"We gotta finish our report for tomorrow," Jess let her know, pulling out his book.

"Library after school?" Rory asked, placing her book on the table.

"Sure, I'll wait outside after school for you," Jess replied.

"Jess, about the party.…" Rory started, only Jess cut her off.

"Rory it's fine, you don't need to explain anything to me. After all, we're only friends, nothing more." Rory looked down, feeling like Jess had just pulled her heart out and stomped on it.

"Yeah, friends," Rory replied, leaving all her emotions out of it. She got up, took care of her tray, and walked off. Rory knew one thing – she was tired of being just his friend.

Jess got up, leaving his tray on the table. He was trying to shake off the thoughts of Rory's hollow words. He wanted to be more than friends but he was positive that he would screw it up and break her heart. For the rest of the day, Jess didn't pay attention during any of his classes. He'd find someone to bum notes from if he really needed them, but he wasn't all that concerned about it. Just like he told Rory, he was waiting outside for her. Rory climbed into Jess's car and the ride was silent for a few seconds before Rory started to laugh.

"What the hell is so funny?" Jess demanded, slightly glancing at her.

"The fact that I wanted you to protect to me from Tristan and you did and now we can't even be ourselves around each other. Can we just let it go?" Rory didn't want to forget about it, especially the way it made her feel.

"Yeah, but only if you're really okay with it."

"I am, Jess, I miss my best friend." Jess could tell that it pained her to say best friend. But he wasn't going to mention anything about it.

"It's easy to miss me." Jess smirked, making Rory roll her eyes. "I missed you too, Ror."

They had got so immersed in their report on Hemingway that the librarian had to kick them out when it was time to close. Without being asked, Jess drove Rory home. They had missed the last bus by a few minutes. The drive to Stars Hollow was a quiet one but it was a comfortable silence.

"Hey Jess?" Rory asked, breaking the silence.

"Yeah, Ror?" Jess asked, stealing a quick glance at her.

"Thanks for the ride,." Rory told him, letting her nerves get the best of her.

"It was nothing, really. I couldn't have left you stranded in Hartford."

"You could've. It's not like I would have been left to sleep in the streets. I would've either stayed at my grandparents' house, took a cab home or called my mom," Rory pointed out just as Jess parked in her driveway.

"Tell me, Rory. Do you have enough money on you for a cab?" Rory shook her head, realizing she only had a handful of change on her. "Would you really stay at your grandparents' house?" Once again Rory shook her head. She wasn't very fond of staying at their house when she didn't have to. "Last but not least, how would you call your mom?" Rory gave him a small glare. Jess really knew her. She had been in a rush this morning and forget her pager on her desk.

"Must you know everything?" Rory asked, getting out of his car.

"Of course." Jess smirked, making Rory stick her tongue out at him. "See ya, Ror," Jess called. Rory turned around from her porch to give him a small wave.

"That can't be my daughter," Lorelai exclaimed, hearing the front door open and close.

"Nope, just some strange teenager," Rory called back, going to her room. "Sorry I didn't call or anything. Got caught up with the report that's due tomorrow," Rory explained, joining her mom on the couch.

"Don't let it happen again. Okay, kid?"

"You got it."

After dropping Rory off, Jess had gotten an idea. His destination was a short drive away; he didn't even have to leave Stars Hollow. Turning off his car, Jess got out, pocketing his car keys. Taking a deep breath, he walked into the empty diner.

"We're closed," Luke called out, not looking up from wiping the counter off.

"I can read, Uncle Luke," Jess replied, sitting on a stool.

"Jess, uh, hi. What brings you by?" Luke was surprised that Jess came here to see him. For the last few years they would meet up in Hartford once a week.

"I was bringing Rory home. Got a bit caught up in our homework."

"You know Rory?" Luke asked, his suspicion coming true.

"Best friends." Luke had caught how strained the words were.

"Right, right. So, uh, do you need something? It's not like you to just to stop in and say hi."

"Oh Jeez, Luke, you caught me," Jess replied, with sarcasm dripping from every word. Luke gave him a pointed look. "Actually, there is something." The way the words slipped out of Jess's mouth had Luke's attention.

"What's wrong, Jess?" Luke asked, full of concern for his nephew. Jess quickly explained his family problems. Luke was taken aback to learn that Jimmy had walked out on them. Luke cursed at himself; he should've knew Jimmy would do something like this. With the things Liz had done after their mom had died, he wasn't all that surprised to learn Liz had fallen off the wagon once again. "I would love to help you out, Jess, but there is no room at my house. I would have to talk to Lorelai about it as well."

"I wasn't asking to move in with you, Luke. More like the apartment upstairs." Jess knew it was huge to ask that of Luke but he didn't have any other choice right now.

"Give me till the weekend to think it over." Luke wanted nothing more than to help Jess out, but having him living above the diner alone was a huge deal, considering he was still a minor. Jess nodded, walking out. Jess had a feeling that Luke wasn't going to open his arms and welcome him in without thinking about it first.


	6. Chapter 6

School and dinner with Emily and Richard went by with very little incident. It might have been the fact that Rory was too absorbed with Jess. All day at school he had been evasive. She couldn't get a straight answer out of him. She tried all day long and by the time the final bell rang Rory was thrilled to head home. Though leaving Jess behind did her no good. Her mind went into over drive about everything that could be wrong with Jess. She crossed everything off when the thought popped into her mind. Jess wasn't one to go out and get drunk. She saw him have a beer or two a few times but she never saw him drunk. She never saw or even heard about him getting high on any drugs. Suicidal was tossed out the window. Something was wrong and she couldn't figure it out. She couldn't go up to him demanding answers, he was entitled to have his secrets. She had no choice but to wait for him to come to her on this.

Jess hated keeping things from Rory. She was the one person that could read him. He really needed to get out of his house. His nights consisted of taking care of his mother, leaving less time to do his work and study. It would only be a matter of time before he was asked to stay after. He had thought about staying late at school to get work done but he then remembered that he needed to be at home to clean up from his mother's mess well he was at school . He needed to be away from Hartford and Stars Hollow. He needed to be far away. New York would do. He had been there when he was a kid, he wanted to go back. He couldn't go alone. He already felt alone and cold in this world unless he was with Rory. With her he felt alive. He wanted to take this journey with her. He was tired of being alone.

Rory sat on the bridge early Saturday morning, a book in hand. She tried to read the words that were spread out before her but her mind was still on Jess. She didn't want to be at home. Her mother was leaving for the night to some weekend spa with Sookie. It was said that Sookie needed the time away from Davey. Jackson had insisted that she go. He wanted Sookie to go relax and have fun, something that she hadn't been able to do since Davey was born 6 months ago. That left Rory home with Luke until Monday.

"I figured I'd find you some where off by yourself." Rory looked up to see Jess walk onto the bridge, joining her. "What am I doing here?"

"That is the million dollar question, so why are you here? Better yet, how did you find me?" Rory placed her book on the bridge beside her.

"You weren't home and your neighbor, the loud one with the gnomes, told me to check at Luke's. From there I was directed to this bridge. Wanna take a trip with me?" He had gone by Rory's house but he never made it to Luke's. Rory had told him about spending time at the bridge reading. The night he had asked Luke to move into the apartment above the diner, he had found his way to this bridge. But no one needed to know that.

"A trip? Where to? How long?" Rory's excitement was getting the best of her.

"Yes, New York, we can come back Monday since school is out till Tuesday. So what do you say?" To Rory that sounded a little out there but it was a risk she wanted to take. It wouldn't be that hard to convince Luke to let her go. Luke was in charge this weekend. Lorelai would trust his judgment on this.

"I want to, I really do, but I need to talk to Luke about it first." Jess had forgotten that Rory had a family that cared about her. He knew that Luke cared about him as well but he hadn't done much to really prove that as of late. "I would talk to my mom but she's out of town till Monday," Rory rattled off getting to her feet.

"Sure thing," Jess replied with half a smile, getting up. He picked Rory's book up, putting it in his back pocket. He had finished his latest book and he had yet to pick a new book out to read.

"Come on, I need coffee anyway and Luke does have the best coffee around."

"So I've been told," Jess smirked, flinging his arm around Rory. He really wanted to see bag boy squirm seeing him with Rory. Jess's smirk grew into a very smug one, feeling Rory's arm snake around his waist. A low growl slipped out of Dean's throat as he watched Rory and Jess walk past Doose's.

"Luke, can I ask you a question?" Rory asked, sitting on a stool at the counter, Jess right beside her.

"What can I do ya for, Rory?" Luke asked, glancing quickly at Jess.

"I think you should go fishing this weekend. You never go anymore since you and Mom got married. I know how you like being in the woods for a weekend. You've closed down the diner before. Why not go this weekend, Luke?"

"You know, it would do me some good to get back out there. Your mom goes on and on about everything, I haven't found the time to go camping and fishing. But I can't leave you alone," He shook his head at the thought. He promised Lorelai that he would be there to watch Rory all weekend. He couldn't just take off.

"I'll be fine. It is Stars Hollow, after all." Rory had every intention of asking if she could go with Jess to New York. She didn't want to lie to him but she found it easier to go around his back on this. It pained her to do this but the rush of lying was taking over her body and she couldn't stop the words from coming out.

"You sure you're gonna be okay?" Rory nodded her head. A polite smile graced her lips. "You know what? I'll do it. I'm gonna close early and take off in the late afternoon." He could get Lorelai to understand. Lorelai had told him that he didn't have to watch Rory all weekend. He could do this.

"I've got homework to do with Jess at home. Can I get a coffee for the walk home?"

"You, like your mother, are asking for an early death." Luke filled a to-go cup, handing it to Rory along with a bag. "Two cherry Danishes. Your mom wanted some this morning before she left, made you some as well."

"Thanks, Luke," Rory replied, jumping off her stool. "Did you want anything, Jess?"

"Nah, I'm good. I'm not addicted to coffee like you." Rory rolled her eyes in a playful way. Shoving him, she gave Luke a wave and headed out the door behind Jess. "I didn't hear you ask if you could go with me."

"I didn't want him to say no only for me to go behind his back. This way it's our little secret."

"Rory Gilmore being devious," Jess smirked, bumping into her lightly. "I like it." The fact she could be that manipulative to get what she wanted made him fall that much more for her. He never thought he would see this side to her. "Homework?" He questioned.

"I'm gonna be running around New York this weekend, I need to get my work done for my story to work." He did have his school bag, it would be nice to have a chance to get some work done.

They sat at the kitchen table doing work for an hour before they made their way to the living room to get comfortable as they worked. Rory had finished her work before Jess. She let him be and went to her room to pack a bag for her little trip with Jess. As time got closer for them to leave, Rory was starting to freak out about being alone with Jess in New York. Rory put on a brave face for Luke. After a million questions from Luke and Rory assuring him she would be fine, he finally left. Rory had explained that if she wasn't home when Babette checked up on her, she was probably in Hartford with a few friends from school. With the coast clear, they hit the road for their weekend get-a-way.

"Are you okay?" Jess asked after a few minutes on the road.

"Nervous. I've only been to New York with my mom," Rory explained with only half the truth. She couldn't admit to him that she was nervous about spending the next few nights with him alone. She didn't want something to happen between them that they would regret, or worse yet, they would do something that ruined their friendship for good.

"It's going to be okay, Rory. If we get lost we'll be together," Jess joked trying to make Rory smile.

"Getting lost is only the start to an amazing journey." Getting lost in the city was the exciting part. Not knowing what was going to happen or the fact she was doing this behind her mom's back was a horrible feeling to have. She shouldn't be doing this, she should have asked her mom if it was okay she went. "I can't do this, Jess!" Rory yelled, worry etched on her face.

"Why not? Everything was okay just a minute ago. You talked Luke into going out of town so you could come with me. What's the matter?" Jess had pulled the car over so he could look at Rory.

"I can't be doing this with out my mom's permission. It's not right." She didn't want to be in this tangled web of a lie she had created.

"We can go back if you really want to or we can keep driving to New York and have ourselves an adventure. On Monday you can have all the guilt in the world. It's up to you, Rory."

"New York." She didn't want Jess to think any less of her. Running off to New York may not be the best choice she has ever made, but she felt she needed to do this. It didn't mean she couldn't feel bad for doing this. She could sit her mom down on Monday and tell her everything. Then she would proceed to ground herself. She had all weekend to come up with the perfect punishment. "I'm sure about this," she told Jess, seeing the questioning look on his face. He nodded, pulling back onto the road. The Clash filled the silence of the car.


	7. Chapter 7

Rory sat on her bed in the hotel room nursing her cup of coffee from the small café around the corner from the hotel they were staying at. When they got into the city they had decided that it was best they get a hotel room for their stay. Jess had walked Rory to the café knowing she needed some caffeine in her. Once in their room which consisted of two full size beds, Jess locked himself in the bathroom to take a shower leaving Rory alone to her thoughts.

She knew that coming to New York was the wrong decision to make, she just didn't want to come off as a goody-goody to Jess. She could go behind her mom's back and do things. She could live on the dangerous side of life. The guilt would go away with time, it just had to. She would prove to herself that she could have fun this weekend and not focus on the part that she had to scam Luke to come here.

"You alright, Rory?" Jess asked walking out of the bathroom, using the towel to dry his hair. With a quick glance he could see something was off with her.

"Uh, yea. Just getting over my guilt for what I did to Luke," Rory told him putting a smile on her face. "What are we going to do first?" Rory asked with hopeful eyes.

"I was thinking that we could go to this really cool pizza place for dinner and tomorrow the real adventure begins," Jess replied digging through his bags for some hair gel.

"I like that." She was far too tired to even see New York tonight. And she was getting hungry. "Jess?" Rory asked with a small voice.

"What's up?" Jess asked stopping at the bathroom door.

"I like your hair just the way it is." Jess smirked seeing the small blush appear on Rory's cheek from what she had just admitted.

"Huh," was Jess's reply before walking back into the bathroom shutting the door. He looked in the mirror a smile tugging at the corners of his mouth. If Rory liked it that way, he'd leave it that way. He emerged a few seconds later without any hair gel in his hair. "Ready?" Jess asked.

"How can I be ready? You've done nothing but hog the bathroom since we got here," Rory retorted slipping into the bathroom. Jess shook his head a little and sat on the bed Rory hadn't claimed.

This weekend would be hard for him. Rory was off-limits. Rory was his step-cousin, it would be too messed up for him to even pursue her but there was just something about her that made him want more. This weekend wasn't about getting together with Rory, it was about needing to be away from his messed up life. He had no problem coming alone, he was afraid that he wouldn't have went back if Rory hadn't come with him. He didn't even tell his mom he was leaving all weekend. He didn't even think she'd notice he was gone. With a drunk for a mom he was able to swipe not only a credit card but a handful of cash as well. Liz wouldn't notice, even when the bill for the credit card came, he'd make a story up, if he was still there. At first he was sad that his parents didn't want him but that sadness turned into anger he held against them. If they wanted to act like they didn't have a kid then why in the hell did they have one for?

"Yo, Jess," Rory said pushing on his shoulder. "Are you in there?"

"Yeah, sorry about that. Ready?" He asked standing up.

"I've been ready for a few minutes now. Where did you go?" Rory asked following him out the door.

"No where. Traffic can be a bitch here, the pizza place is with in walking distance, it's not far I promise."

"I don't mind, really." Rory gave him a reassuring smile as they walked out into the busy world of New York City. "Jess, are you okay?" Rory asked sensing that something was bugging him.

"Just peachy," Jess replied with just a tad too much sarcasm.

"You can talk to me, Jess."

"You wouldn't understand, Rory. You have this perfect life." Jess snapped.

"That's not even close to being true." Rory stopped pulling on Jess's arm to get him to stop.

"Rory, don't!" Jess warned looking down at her

"Try me, Jess!" Rory exclaimed matching the intensity Jess had in his eyes.

"Can we talk about this later? I'm kinda starving and I don't have the energy to have a yelling match with you in the middle of the sidewalk, where a bunch of strangers can hear my problems." Rory nodded feeling guilty about trying to start a fight with Jess in public.

"Of course and I'm sorry." Jess was quick to pull her in for a hug.

"You have no reason to be sorry, Rory."

"If you say so, now where's this pizza place?" Rory asked with excitement.

"It's Lombardi's Pizza, just a block away," Jess replied with amusement.

They got their pizza to go. Much to Jess's dignity, Rory paid for the pizza. She claimed that since it was the 21st century and they weren't on a date she had every right to pay. It didn't help that Jess had forgotten his wallet in his other jeans back at the hotel. Jess had grabbed the pizza and carried it back. They stopped at a vending machine and got something to drink before they retreated back to their rooms.

"I'll pay you back, Rory," Jess told her as they got situated at the little table in the room.

"I know, Jess. We gotta eat tomorrow," Rory replied making Jess roll his eyes. "I do want a hot dog from a vendor on the street. No make it 2 or even 3," Rory beamed making Jess chuckle.

"As you wish. But I do have one spot in mind. You'll like it," Jess bumped her knee under the table with his own.

"Where's that?" Rory asked with big puppy dog eyes.

"It's a surprise, Ror."

"Tell me, tell me, tell me, please," Rory pleaded with him bouncing in her seat. She even stuck her bottom lip out to pout.

"No can do. Now eat before I eat it all," Jess told her pointing at the pizza. It took him everything he had not to burst out in laughter at her actions.

"You wouldn't dare," Rory told him with a glare.

"Try me," Jess replied with a smirk.

"No," Rory answered him. She dug back into the pizza. Jess gave her a look of bewilderment before digging back into his slice.

After they finished off the pizza, more so Rory than Jess they got ready for bed. They both got comfortable on their own bed. Rory was already exhausted from the day she had. She turned her back to not only Jess but to the TV that Jess had turned on. Jess seeing that Rory was out cold turned the TV down and settled into his own bed waiting for sleep to over come him.


End file.
